IE892233L - Process for the production of¹o2,2'-anhydro-1-(beta-d-arabinofuranosyl)thymine - Google Patents

Process for the production of¹o2,2'-anhydro-1-(beta-d-arabinofuranosyl)thymine

Info

Publication number
IE892233L
IE892233L IE892233A IE223389A IE892233L IE 892233 L IE892233 L IE 892233L IE 892233 A IE892233 A IE 892233A IE 223389 A IE223389 A IE 223389A IE 892233 L IE892233 L IE 892233L
Authority
IE
Ireland
Prior art keywords
beta
arabinofuranosyl
anhydro
thymine
of1o2
Prior art date
Application number
IE892233A
Other versions
IE65735B1 (en
Inventor
Charles William Murtiashaw
Original Assignee
Martin Francis Finn
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Martin Francis Finn filed Critical Martin Francis Finn
Publication of IE892233L publication Critical patent/IE892233L/en
Publication of IE65735B1 publication Critical patent/IE65735B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/09—Pyrimidine radicals with arabinosyl as the saccharide radical

Abstract

In the disclosed process, an O<2>,2 min anhydro-1-( beta -D-arabinofuranosyl)thymine is formed by condensing a 2-amino- beta -arabinofurano[1 min ,2 min :4,5,]-2-oxazoline with a compound of the formula <CHEM> wherein R1 is C1-C4 alkyl; X is halogen or OR2, wherein R2 is H, C1-C4 alkyl or phenyl; in the presence of a suitable solvent at about 0 DEG C to about 150 DEG C. Catalytic agents such as dimethylaminopyridine and triethylamine may also be added to accelerate the reaction. Protected intermediates of the anhydronucleosides and aminooxazolines are also disclosed.
IE223389A 1988-07-12 1989-07-11 Process for the production of O2,2'-anhydro-1-(beta-D-arabinofuranosyl)thymine IE65735B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/217,906 US5008384A (en) 1988-07-12 1988-07-12 Process for the production of O.sup. 2,2'-anhydro-1-(β-D-arabinofuranosyl)thymine

Publications (2)

Publication Number Publication Date
IE892233L true IE892233L (en) 1990-01-12
IE65735B1 IE65735B1 (en) 1995-11-15

Family

ID=22812966

Family Applications (1)

Application Number Title Priority Date Filing Date
IE223389A IE65735B1 (en) 1988-07-12 1989-07-11 Process for the production of O2,2'-anhydro-1-(beta-D-arabinofuranosyl)thymine

Country Status (21)

Country Link
US (1) US5008384A (en)
EP (1) EP0351126B1 (en)
JP (1) JPH075626B2 (en)
KR (1) KR910008112B1 (en)
CN (1) CN1039423A (en)
AT (1) ATE117314T1 (en)
AU (1) AU603042B2 (en)
CA (1) CA1315776C (en)
DD (2) DD292003A5 (en)
DE (1) DE68920648T2 (en)
DK (1) DK342189A (en)
ES (1) ES2066853T3 (en)
FI (1) FI893364A (en)
GR (1) GR3015293T3 (en)
HU (1) HUT50843A (en)
IE (1) IE65735B1 (en)
IL (1) IL90884A0 (en)
NO (1) NO892821L (en)
PT (1) PT91113B (en)
YU (1) YU138789A (en)
ZA (1) ZA895259B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992009599A1 (en) * 1990-11-30 1992-06-11 Yamasa Shoyu Kabushiki Kaisha PROCESS FOR PRODUCING 1-(2,3-DIDEOXY-β-D-glycero-PENT-2-ENOFURANOSYL)THYMINE
ES2125408T3 (en) * 1994-05-20 1999-03-01 Council Scient Ind Res A PROCEDURE FOR THE PREPARATION OF BETA-THYMIDINE.
JP3942414B2 (en) 2000-11-29 2007-07-11 三井化学株式会社 L-type nucleic acid derivative and synthesis method thereof
MXPA03008870A (en) * 2001-03-30 2004-01-29 Triangle Pharmaceuticals Inc Process for the preparation of 2 -halo-$g(b)-l-arabinofuranosyl nucleosides.
DE10216426A1 (en) * 2002-04-12 2003-10-23 Boehringer Ingelheim Pharma Beta-L-2'-deoxy-thymidine preparation, for use as antiviral agent, from L-arabinose in 4-stage process via new oxazolidine derivative and thymidine derivative intermediates
CN1812995A (en) 2003-04-28 2006-08-02 艾登尼科斯（开曼）有限公司 Industrially scalable nucleoside synthesis
WO2005003374A2 (en) 2003-06-30 2005-01-13 Idenix (Cayman) Limited SYNTHESIS OF β-L-2-DEOXY NUCLEOSIDES
AU2007224441A1 (en) 2006-03-15 2007-09-20 Novartis Ag Process for preparing L-nucleic acid derivatives and intermediates thereof
CN102014919B (en) 2008-03-03 2015-02-25 托斯克公司 Methotrexate adjuvants to reduce toxicity and methods for using the same

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322747A (en) * 1965-04-01 1967-05-30 Merck & Co Inc Thionocarbonate nucleosides
US3463850A (en) * 1967-01-03 1969-08-26 Merck & Co Inc Arabinofuranosyl 2-thiopyrimidines and pharmaceutical compositions thereof
US3658788A (en) * 1969-06-06 1972-04-25 Salk Inst For Biological Studi Aminooxazolines and products thereof and processes for synthesizing same
US3709874A (en) * 1970-03-19 1973-01-09 Syntex Corp 1-beta-d-arabinofuranosyl cytosine derivatives and methods of preparing
US3812098A (en) * 1970-03-19 1974-05-21 Syntex Inc O2,2'-anhydro-1-(beta-d-arabinofuranosyl)-cytosine derivatives and methods of making and related procedures
US3792040A (en) * 1970-03-19 1974-02-12 Syntex Corp Acyl derivatives of o2,2'-anhydro-1-(beta-d-arabinofuranosyl)-cytosines and methods of preparing
US3920630A (en) * 1970-09-24 1975-11-18 Upjohn Co 2,2{40 -Anhydro-ara-cytidine compounds and process of preparation
SE391183B (en) * 1971-04-15 1977-02-07 Asahi Chemical Ind 2 ', 3'-O-SULFINYLCYTIDINE AND ACID ADDITIONAL SALTS THEREFORE FOR USE AS AN INTERMEDIATE FOR THE PREPARATION OF 2,2'-ANHYDRO- (1-BETA-D-ARABINOFURANOSYL) CYTOSIN
US3978042A (en) * 1975-01-31 1976-08-31 The Upjohn Company Process for preparing cyclocytidine derivatives
US4140850A (en) * 1977-08-29 1979-02-20 The Upjohn Company 2,2'-Anhydrotriazine nucleosides and process for preparing the same
JPS5649398A (en) * 1979-09-28 1981-05-02 Yamasa Shoyu Co Ltd Preparation of 1-beta-d-arabinofuranosyl-2,2'-cyclothymine
JPS636557A (en) * 1986-06-26 1988-01-12 Sharp Corp Formation of fine pattern

Also Published As

Publication number Publication date
EP0351126B1 (en) 1995-01-18
NO892821L (en) 1990-01-15
DE68920648T2 (en) 1995-05-18
IL90884A0 (en) 1990-02-09
JPH075626B2 (en) 1995-01-25
DK342189A (en) 1990-01-15
GR3015293T3 (en) 1995-06-30
AU3802089A (en) 1990-04-26
AU603042B2 (en) 1990-11-01
DD292003A5 (en) 1991-07-18
KR910008112B1 (en) 1991-10-10
CA1315776C (en) 1993-04-06
JPH0259598A (en) 1990-02-28
PT91113B (en) 1995-01-31
KR900001704A (en) 1990-02-27
CN1039423A (en) 1990-02-07
DE68920648D1 (en) 1995-03-02
PT91113A (en) 1990-02-08
YU138789A (en) 1990-12-31
ATE117314T1 (en) 1995-02-15
EP0351126A3 (en) 1990-10-24
EP0351126A2 (en) 1990-01-17
DK342189D0 (en) 1989-07-11
ZA895259B (en) 1991-02-27
FI893364A (en) 1990-01-13
HUT50843A (en) 1990-03-28
US5008384A (en) 1991-04-16
FI893364A0 (en) 1989-07-11
DD284024A5 (en) 1990-10-31
NO892821D0 (en) 1989-07-07
IE65735B1 (en) 1995-11-15
ES2066853T3 (en) 1995-03-16

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Legal Events

Date Code Title Description
MM4A Patent lapsed